DE1593428B2 - Verfahren zur reinigung von betalactonen mit zwei wasserstoffatomen am beta-kohlenstoffatom und einer oder zwei alkylgruppen mit hoechstens 4 kohlenstoffatomen am alpha-kohlenstoffatom - Google Patents
Verfahren zur reinigung von betalactonen mit zwei wasserstoffatomen am beta-kohlenstoffatom und einer oder zwei alkylgruppen mit hoechstens 4 kohlenstoffatomen am alpha-kohlenstoffatomInfo
- Publication number
- DE1593428B2 DE1593428B2 DE19661593428 DE1593428A DE1593428B2 DE 1593428 B2 DE1593428 B2 DE 1593428B2 DE 19661593428 DE19661593428 DE 19661593428 DE 1593428 A DE1593428 A DE 1593428A DE 1593428 B2 DE1593428 B2 DE 1593428B2
- Authority
- DE
- Germany
- Prior art keywords
- lactone
- weight
- percent
- carbon
- pressure
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000000746 purification Methods 0.000 title claims description 3
- 229910052799 carbon Inorganic materials 0.000 title claims 6
- -1 HYDROGEN ATOMS Chemical group 0.000 title claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title 3
- 150000002596 lactones Chemical class 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 8
- 229960000380 propiolactone Drugs 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 238000004140 cleaning Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims 6
- 150000002513 isocyanates Chemical class 0.000 claims 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- 150000002736 metal compounds Chemical class 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000012535 impurity Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 2
- 239000004814 polyurethane Substances 0.000 claims 2
- 229920002635 polyurethane Polymers 0.000 claims 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims 1
- FYHBVTYDATZUEE-UHFFFAOYSA-N 3-bromo-2,2-dimethylpropanoic acid Chemical compound BrCC(C)(C)C(O)=O FYHBVTYDATZUEE-UHFFFAOYSA-N 0.000 claims 1
- PGSWEKYNAOWQDF-UHFFFAOYSA-N 3-methylcatechol Chemical compound CC1=CC=CC(O)=C1O PGSWEKYNAOWQDF-UHFFFAOYSA-N 0.000 claims 1
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 claims 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims 1
- 229910052776 Thorium Inorganic materials 0.000 claims 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229960004217 benzyl alcohol Drugs 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 claims 1
- 239000012975 dibutyltin dilaurate Substances 0.000 claims 1
- 125000005442 diisocyanate group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000002349 favourable effect Effects 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000009413 insulation Methods 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910001507 metal halide Inorganic materials 0.000 claims 1
- 150000005309 metal halides Chemical class 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 229920001228 polyisocyanate Polymers 0.000 claims 1
- 239000005056 polyisocyanate Substances 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 229940096992 potassium oleate Drugs 0.000 claims 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000003860 storage Methods 0.000 claims 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6511922A NL6511922A (enrdf_load_stackoverflow) | 1965-09-14 | 1965-09-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1593428A1 DE1593428A1 (de) | 1970-01-08 |
| DE1593428B2 true DE1593428B2 (de) | 1973-03-29 |
| DE1593428C3 DE1593428C3 (enrdf_load_stackoverflow) | 1973-10-25 |
Family
ID=19794134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593428 Granted DE1593428B2 (de) | 1965-09-14 | 1966-09-12 | Verfahren zur reinigung von betalactonen mit zwei wasserstoffatomen am beta-kohlenstoffatom und einer oder zwei alkylgruppen mit hoechstens 4 kohlenstoffatomen am alpha-kohlenstoffatom |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3576824A (enrdf_load_stackoverflow) |
| BE (1) | BE686743A (enrdf_load_stackoverflow) |
| CH (1) | CH468996A (enrdf_load_stackoverflow) |
| DE (1) | DE1593428B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1087287A (enrdf_load_stackoverflow) |
| NL (1) | NL6511922A (enrdf_load_stackoverflow) |
| SE (1) | SE306527B (enrdf_load_stackoverflow) |
-
1965
- 1965-09-14 NL NL6511922A patent/NL6511922A/xx unknown
-
1966
- 1966-09-12 SE SE12248/66A patent/SE306527B/xx unknown
- 1966-09-12 DE DE19661593428 patent/DE1593428B2/de active Granted
- 1966-09-12 GB GB40668/66A patent/GB1087287A/en not_active Expired
- 1966-09-12 BE BE686743D patent/BE686743A/xx unknown
- 1966-09-12 CH CH1313266A patent/CH468996A/de unknown
-
1968
- 1968-11-18 US US779301A patent/US3576824A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL6511922A (enrdf_load_stackoverflow) | 1967-03-15 |
| DE1593428A1 (de) | 1970-01-08 |
| CH468996A (de) | 1969-02-28 |
| DE1593428C3 (enrdf_load_stackoverflow) | 1973-10-25 |
| US3576824A (en) | 1971-04-27 |
| GB1087287A (en) | 1967-10-18 |
| BE686743A (enrdf_load_stackoverflow) | 1967-03-13 |
| SE306527B (enrdf_load_stackoverflow) | 1968-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |